(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate | 1217184-42-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate
• 英文别名: β-caryolanyl acetate；[(1S,2S,5R,8R)-4,4,8-trimethyl-1-tricyclo[6.3.1.02,5]dodecanyl] acetate
• CAS: 1217184-42-3
• 化学式: C₁₇H₂₈O₂
• 分子量: 264.408
• InChiKey: SJDDHMSVZMBJPH-WTTBNOFXSA-N

物化性质

• 沸点：
  295.9±8.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  β-caryophyllene 、 乙酸酐 在 三氟化硼乙醚 作用下， 以 乙醇 为溶剂， 以20%的产率得到(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate
  参考文献：
  名称：

  Synthesis of novel acetates of β-caryophyllene under solvent-free Lewis acid catalysis

  摘要：

  Acylation of -caryophyllene, a sesquiterpene hydrocarbon with acetic anhydride, was carried out under mild catalytic conditions using Lewis acids such as BF3 center dot Et2O, ZnCl2, FeCl3, I2 and AlCl3 as catalysts. Among these, BF3 center dot Et2O was found to catalyse the reaction most efficiently, yielding three acylated products in 75% yield under solvent-free conditions. The structures were confirmed by NMR and MS techniques.

  DOI：

  10.1080/14786410903031500

文献信息

• Heteropoly acid catalysts in the valorization of the essential oils: Acetoxylation of β-caryophyllene
  作者：Kelly A. da Silva Rocha、Nathália V.S. Rodrigues、Ivan V. Kozhevnikov、Elena V. Gusevskaya

  DOI：10.1016/j.apcata.2009.11.032

  日期：2010.2

  efficient and clean method for the synthesis of 2, providing a mixture containing two stereoisomeric β-caryolanyl acetates 2a and 2b, 2a/2b = 80/20 mol/mol, with 100% GC yield, has been developed using PW as a homogeneous catalyst under mild reaction conditions. The reaction occurs at 25 °C with a catalyst turnover number of 2000. The catalyst can be recovered without neutralization and reused without loss

  H 3 PW 12 O 40（PW）是Keggin系列中最强的杂多酸，是一种活性且环境友好的催化剂，用于将β-石竹烯（1）液相转化为乙酸-β-戊烯基乙酸酯（2）异构系统。一种高效且清洁的合成2的方法，提供了包含两种立体异构体的β-羧甲基乙酸乙酸酯2a和2b，2a / 2b的混合物 在温和的反应条件下，使用PW作为均相催化剂已开发出= 80/20 mol / mol，GC产率为100％。该反应在25℃下进行，催化剂的周转数为2000。该催化剂无需中和就可以回收，并且可以在不损失活性和选择性的情况下重复使用。